Thallium(III) p-Tosylate Mediated Oxidative 2,3-Aryl Rearrangement: A New Useful Route to Ipriflavone and Its Analogs

REFERENCES

• (a) Ingham , J. L. In Phytoalexins ; I. A. Baily , J. W. Mansfield (Eds.); Blackie : Glasgow and London , 1982 ; p. 21 ; (b) Ingham, J. L. Naturally occurring isoflavonoids (1855–1981). Prog. Chem. Org. Nat. Prod. 1983, 43(1), 1–266; (c) Dewick, P. M. In The Flavonoids: Advances in research since 1986” J. B. Harborne, (Ed.); Chapman & Hall: London, 1993; p. 149; (d) Dixon, R. A. In Comprehensive Natural Products Chemistry; D. H. R. Barton, R. Nakanishi (Eds.); Elsevier: Oxford, 1999; vol. 1, p. 773 .
   Google Scholar
• Miksicek , R. J. Estrogenic flavonoids: Structural requirements for biological activity . Proc. Soc. Exp. Biol. Med. 1995 , 208 ( 1 ), 44 – 50 .
   PubMed Web of Science ®Google Scholar
• Yanagihara , K. ; Ito , A. ; Toge , T. ; Numoto , M. Antiproliferative effects of isoflavones on human cancer cell lines established from the gastrointestinal tract . Cancer Res. 1993 , 53 ( 23 ), 5815 – 5821 .
   PubMed Web of Science ®Google Scholar
• Bandyukova , V. A. ; Cherevatye , V. S. ; Ozimina , I. I. ; Andreeva , O. A. ; Lebedava , A. L. ; Davydov , V. S. ; Vashchenko , T. N. ; Postnikova , N. V. Antibacterial activity of flavonoids of some flowering plant species . Rastit Resur. 1987 , 23 , 607 – 612 .
   Google Scholar
• El-Gammal , A. A. ; Mansour , R. M. Antimicrobial activities of some flavonoid compounds . Zentralbl Mikrobiol. 1986 , 141 ( 7 ), 561 – 565 .
   PubMedGoogle Scholar
• Takai , M. ; Yamaguchi , H. ; Saitoh , T. ; Shibata , S. Chemical studies on the oriental plant drugs XXXV: The chemical constituents of the Heartwood of Maackia amurensis . Var. Buergeri. Chem. Pharm. Bull. 1972 , 20 , 2488 – 2490 .
   Web of Science ®Google Scholar
• Akiyama , T. ; Ishida , J. ; Nakagawa , S. ; Ogawara , H. ; Watanabe , S. ; Itoh , N. ; Shihuya , M. ; Fukami , Y. Genistein, a specific inhibitor of tyrosine-specific protein kinases . J. Biol. Chem. 1987 , 262 ( 12 ), 5592 – 5595 .
   PubMed Web of Science ®Google Scholar
• Nogradi , M. The ipriflavone story (1969–1993) . Khem. Kozl. 1993 , 77 ( 1 ), 55 – 58 .
   Google Scholar
• (a) Kleemann , A. ; Engel , J. Pharmaceutical Substances: Synthesis, Patents, Applications, , 4th ed. ; Georg Thieme Verlag , Stuttgart and New York , 2001 ; 1094 ; (b) Elks, J.; Ganellin, C. R. Dictionary of Drugs; Chapmann and Hall: London, 1991; p. 651; (c) Vincent, A.; Fitzpatrick, L. A. Soy isoflavones: Are they useful in menopause? Mayo Clin. Proc. 2000, 75, 1174–1184, and references cited therein .
   Google Scholar
• (a) Kunikata , K. ; Fukunaga , K. Method for the preparation and purification of 7-isopropoxyisoflavone. JP Patent 09268187 , Jpn. Kokai Tokkyo Koho. 1997 ; (b) Imamiya, K.; Kawamoto, H. Preparation of 7-isopropoxyisoflavone from 7-hydroxyisoflavone and isopropyl sulfonates. JP 11012265, Jpn. Kokai Tokkyo Koho. 1999 .
   PubMedGoogle Scholar
• (a) Feuer , L. ; Nogradi , M. ; Gottsegen , A. ; Vermes , B. ; Streliszky , J. ; Wolfner , A. ; Farkas , L. ; Antus , S. ; Kovacs , M. Isoflavone derivatives as feed additives . Ger. Offen. 2 , 125 , 245 , 1972 ; (b) Kallay, T.; Lanyi, G.; Ledniczky, L.; Imrei, L.; Hoffmann, G.; Sziladi, M.; Somfai, E.; Montay, T. An improved process for the preparation of substituted isoflavone derivatives. PCT Int. Appl. WO 9115483, 1991; (c) Nogradi, M.; Gottsegen, A.; Antus, S.; Streliszky, J.; Vermes, B.; Wolfner, A.; Major, A.; Szuels, J.; Bendeffy, J.; Marmarosi, T. Isoflavone derivatives. PCT Int. Appl. WO 9503,293, 1995; (d) Kunikata, K.; Fukunaga, K. Preparation and purification of 7-hydroxy isoflavone as pharmaceutical intermediate. JP 09157268, Jpn. Kokai Tokkyo Koho. 1997 .
   Google Scholar
• Orjales-Venero , A. ; Canal-Mori , G. ; Mosquera-Pestana , R. Process for the preparation of 7-isopropoxyisoflavone. ES 2072802, Span 1995.
   Google Scholar
• Singh , O. V. ; Garg , C. P. ; Kapoor , R. P. Oxidative 1,2-aryl rearrangement in flavanones using thallium(III) p-tolyl sulphonate (TTS): A new useful route to isoflavones . Tetrahedron Lett. 1990 , 31 ( 19 ), 2747 – 2750 .
   Web of Science ®Google Scholar
• Singh , O. V. ; Kapil , R. S. A general method for the synthesis of isoflavones by oxidative rearrangement of flavanones using thallium(III) perchlorate . Indian J. Chem. 1993 , 32B ( 9 ), 911 – 915 .
   Google Scholar
• Singh , O. V. ; Muthukrishnan , M. ; Sundaravadivelu , M. Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate . Indian J. Chem. 2005 , 44B ( 12 ), 2575 – 2581 .
   Google Scholar
• Kazuhiko , I. ; Hitoshi , T. ; Kazuo , I. ; Toshihiro , T. ; Mizuo. Synthesis of Helilandin B, pashanone, and their isomers . J. Nat. Prod. 1988 , 51 ( 5 ), 906 – 914 .
   PubMed Web of Science ®Google Scholar
• Singh , O. V. ; Kapil , R. S. A new route to 2-aryl-4-quinolones via thallium(III) p-tolylsulfonate–mediated oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones . Synth. Commun. 1993 , 23 ( 3 ), 277 – 283 .
   Web of Science ®Google Scholar